144 Winchester St, Brookline, MA 02446
663W521faefa1d61c
663W521faf2623638
OFF MARKET

$2,785,300

Trulia Estimate
  • 4 Beds
  • 1 Bath
  • 3,984 sqft

144 Winchester St, Brookline, MA 02446

Corey Hill
Est. Refi. Payment $16,571/mo*
Refinance Your Home

Home Value

Trulia Estimate
$2.79M
Since last month
Decreased$51K (-1.8%)
Since last year
Increased$150K (+5.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +41% in the last 10 years
MonthEstimated value
2026
August 2026$2.79M
August 2026$2.78M
July 2026$2.84M
June 2026$2.8M
May 2026$2.84M
April 2026$2.75M
March 2026$2.75M
February 2026$2.68M
January 2026$2.68M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1572 Beacon St, Brookline, MA
0.32
Multi-Family Home
$2,200,000
02/02/26
5
3
3,978
65 Atherton Rd, Brookline, MA
0.12
Multi-Family Home
$2,650,000
12/12/25
6
3.5
3,277
126 Westbourne Ter, Brookline, MA
0.45
Multi-Family Home
$2,200,000
06/10/26
6
2
4,369
85 Naples Rd, Brookline, MA
0.39
Multi-Family Home
$4,000,000
03/02/26
6
2
5,481
5 Fiske Ter, Allston, MA
0.30
Multi-Family Home
$1,250,000
12/23/25
5
2
2,644
91 Verndale St, Brookline, MA
0.24
Multi-Family Home
$2,862,500
10/21/25
8
4
4,166
28 Verndale St, Brookline, MA
0.25
Multi-Family Home
$2,250,000
12/12/25
8
5
3,342
589-591 Washington St, Brookline, MA
0.39
Multi-Family Home
$1,800,000
01/13/26
9
4
3,102
63 Green St #65, Brookline, MA
0.51
Multi-Family Home
$3,600,000
05/19/26
8
4
5,568
45 Dwight St, Brookline, MA
0.50
Multi-Family Home
$3,350,000
12/12/25
6
3
7,160

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
138 Winchester St #138, Brookline, MA 02446
0.01
-
3
3.5
2,691
Off Market
197 Mason Ter, Brookline, MA 02446
0.04
$3,084,700
4
3.5
2,480
Off Market
50 Winchester St #101, Brookline, MA 02446
0.06
$1,726,700
2
2
1,669
Off Market
188 Mason Ter #188, Brookline, MA 02446
0.07
$2,475,000
4
3.5
2,585
Recently Sold
186 Mason Ter #186, Brookline, MA 02446
0.07
$2,600,000
4
3.5
2,504
Recently Sold
219 Mason Ter #219, Brookline, MA 02446
0.06
-
4
2.5
2,471
Off Market
2 Thorndike St #2, Brookline, MA 02446
0.05
-
5
5.5
3,880
Off Market
10 Fuller St #3, Brookline, MA 02446
0.07
$1,705,100
4
2
2,228
Off Market
17 Coolidge St, Brookline, MA 02446
0.07
$3,261,000
6
4.5
4,545
Recently Sold
186-188 Mason Ter, Brookline, MA 02446
0.08
-
4
3.5
2,725
Off Market
178 Mason Ter, Brookline, MA 02446
0.09
-
5
4.5
3,800
Off Market
109 Winchester St #8, Brookline, MA 02446
0.08
$637,600
2
1
719
Off Market

Local Information

  • Map ViewExplore the area around 144 Winchester St.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 1900
3,984 sqft
$699/sqft

About this House

(917) 617-9114 - 4 Bd on Winchester St.




Transportation
Subway Lines and Stops
GREEN-C - Brandon Hall (0.3 miles)
GREEN-B - Griggs St. (0.39 miles)
Bus Routes and Stops
66 - Harvard Ave & Commonwealth Ave (0.42 miles)
65 - Washington St & Beacon St (0.45 miles)

No broker fee!

(RLNE1395570)
144 Winchester St, Brookline, MA 02446 is a 4 bedroom, 1 bathroom, 3,984 sqft multi-family in Corey Hill, built in 1900. More recently, it was listed as a rental in April 2015 with an asking price of $4,750 per month. That rental listing was removed on May 15, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,785,300, with a rent estimate of $4,112/month.

Home Details for 144 Winchester St

Interior Features

Interior Details
BasementNumber of Rooms: 17
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Brick

Property Information

Year Built
Year Built: 1900Year Updated: 1971
Property Type / Style
Property Type: Multi FamilyArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 7840 sqft

Price and Tax history

DateEventPrice
May 15, 2015
Source: Agent Provided
ListingRemoved
$4,750
Apr 22, 2015
Source: Agent Provided
Listed For Rent
$4,750

Market trends in Brookline

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.22M
$182KMoM
Sale-to-List Price
99.7%
0.2%MoM
Price per sq ft
$816
$19MoM
Available listings
216
37MoM

Around this home

Neighborhood Overview

Corey Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Corey Hill

At least 48 Trulia users voted on each feature.

  • 100 % Say there are sidewalks

  • 97 % Say it's walkable to grocery stores

  • 96 % Say it's walkable to restaurants

  • 95 % Say it's dog friendly

  • 88 % Say people would walk alone at night

  • 84 % Say streets are well-lit

  • 77 % Say there's wildlife

  • 71 % Say kids play outside

  • 67 % Say there's holiday spirit

  • 62 % Say neighbors are friendly

  • 58 % Say parking is easy

  • 48 % Say they plan to stay for at least 5 years

  • 45 % Say there are community events

  • 45 % Say it's quiet

  • 28 % Say yards are well-kept

  • 22 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Very dog friendly "
    0
    Flag
  • Trulia User
    "I’v stayed in a hotel in this neighborhood. It is a beautiful area with many shops to explore. Hope to move to this area. "
    0
    Flag
  • Pat B.
    "It's dog friendly...there's lots of parks around to take pets."
    0
    Flag
  • Pat B.
    "The commute is pretty easy. The train is pretty reliable around here so it makes getting to and from the area pretty simple. I wish there were more buses though."
    0
    Flag
  • Pat B.
    "The closeness of the transportation is great. All of the major green lines are very close to Corey Hill and it makes getting around very easy."
    3
    Flag
  • Pat B.
    "There's some strange people who are around, but they're harmless. There's lots of daycare places, so if someone has a young kid there's lots of options nearby."
    1
    Flag
  • Tkesav
    "corey hill is near coolidge corner. yoy can see skyline of Boston..close to Trader Joes, Wholefoods, Fenway,."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 144 Winchester St

  • What is 144 Winchester St estimated to be worth?
    Trulia's estimated value for 144 Winchester St in Brookline, MA is $2,785,300.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.22M. That is down $182K from the prior month.
  • What do residents say about the Corey Hill neighborhood?
    Residents describe the Corey Hill neighborhood in Brookline, MA as pedestrian-friendly, walkable to grocery stores, and walkable to restaurants. See recently sold homes in Corey Hill, Brookline.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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Apartments for Rent

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Off Market Homes Near 144 Winchester St

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